Methyl arachidonate → Arachidonyl alcohol

HRID 1373446Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1373446
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9](=O)[CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>CCOCC>[CH2:9]([OH:8])[CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Komponenten

4

Edukt 2

HCID 6421258Methyl arachidonateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 10891603Arachidonyl alcoholAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a magnetically stirred solution of 0.5 ml (0.5 mmol) of LiAlH4 in Et2O, 100 mg (0.314 mmol) of arachidonic acid methyl ester in 2 mL of Et2O was added dropwise at 0° C. The reaction mixture was stirred for 1 h and then quenched by addition of 1 mL of EtOAC. 2 mL of saturated NH4Cl solution was added and the organic layer was separated, dried with MgSO4, filtered and evaporated. Chromatography on silica gel (eluents: CH2Cl2/petroleum ether up to 70% CH2Cl2), evaporation, followed by membrane filtration of a CH2Cl2 solution of the product gave 99.3 mg (0.292 mmol, 93% yield) of arachidonyl alcohol as a colorless oil: TLC (CHCl3) Rf 0.28; 1H NMR (200 MHZ, CDCl3) δ 5.37 (m, 8 H), 3.61 (t, 2 H, J=6 Hz), 2.79 (m, 6H), 2.08 (m, 4 H), 1.66–1.17 (m, 8H), 0.92 (t, 3H, J=7 Hz); Anal. C, H.

Aufarbeitung

  1. customquenched by addition of 1 mL of EtOAC
  2. addition2 mL of saturated NH4Cl solution was added
  3. customthe organic layer was separated
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customChromatography on silica gel (eluents: CH2Cl2/petroleum ether up to 70% CH2Cl2), evaporation
  8. filtrationfollowed by membrane filtration of a CH2Cl2 solution of the product

Quellen und Nachweise

ORD-Eintrag
ord-5900ee2211d943f8a3d0a80e5cd0b58b
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07161016B1

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